N-bromobutanimide → 5-Bromo-2-ethoxybenzoic acid

HRID 78476

반응식

HRID 78476 반응식
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Br:13]N1C(=O)CCC1=O>C(#N)C>[Br:13][C:10]1[CH:11]=[CH:12][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 672522-Ethoxybenzoic acid

생성물 1

HCID 52099205-Bromo-2-ethoxybenzoic acid

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

To a solution of 2-ethoxybenzoic acid (3.3 g, 20.0 mmol) in 75 mL of acetonitrile at 0° C. was added N-bromosuccinimide (3.7 g, 21 mmol) in 15 mL of acetonitrile. The reaction mixture was warmed to ambient temperature and the mixture was allowed to stir for 48 hours. The mixture was quenched with 20 mL of H2O and the layers were separated. The aqueous layer was extracted with three 15 mL portions of CH2Cl2 and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 10% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 262, 264 (M+NH4)+.

후처리

  1. customThe mixture was quenched with 20 mL of H2O
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with three 15 mL portions of CH2Cl2
  4. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification via column chromatography (SiO2, 10% hexanes in ethyl acetate)

출처 및 근거

ORD 기록
ord-f54b14f4a7f9455ea5c050472e4b14fb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841334B2

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